Decision-Making Archives - How to be Awesome at Your Job

Pete Mockaitis
Kyle, welcome!

Kyle Austin Young
Thank you for having me. I’m excited to be here.

Pete Mockaitis
Well, I’m excited to talk about success and numbers, two of my favorite things, Kyle.

Kyle Austin Young
Good for you. This is a good fit.

Pete Mockaitis
Yeah, right. Well, could you start by sharing with us a particularly surprising and fascinating discovery you’ve made as you are putting together this opus, Success is a Numbers Game?

Kyle Austin Young
I think one of the biggest surprises to me was I feel like I’ve been able to stumble into why we see so much failure in our world, why we have stats floating around that nine out of 10 businesses fail, that such a vast majority of people who set New Year’s resolutions, ultimately, won’t accomplish them. We hear that most mergers and acquisitions fail to create lasting value for shareholders. Why does that happen? Ultimately, I think that a lot of people are falling into a really specific thinking trap, and I’ll explain it in the context of an example.

Let’s say that you’ve set the goal of trying to run a marathon, and you hire a running coach who says, “I can get you there, but there’s three things you’re going to have to do. I need you to eat, sleep, and train exactly how I tell you to. I’m going to give you a regimen for each of those three things. And if you do all three of them, you’ll be ready on race day. If you don’t, you’re not going to be able to successfully run such a long distance.”

So, in this goal, we’ve learned that there’s three things that have to go right for us to get what we want. And I think when humans set goals, we instinctively try to get a sense of what’s going to be expected of us, what’s going to be required for us to achieve success. I think that’s something we do naturally. I think we also check in with ourselves and ask the question, “Do I think I can do each of those things?”

In this case, “Do I think I can eat, sleep, and train the way that I’m going to have to?” And we try to get a sense of that. I’m going to layer some numbers on it to illustrate where the thinking trap often occurs. Let’s just say that we think it’s 70% across the board, 70% chance I’ll eat the way I’m supposed to, 70% chance I’ll sleep the way I’m supposed to, 70% chance I’ll train the way that I’m supposed to.

This is where the trap happens. A lot of people fall into this error of averaging. We try to consider what’s going to have to go right in order to get what we want, and if we feel good about the individual prerequisites, we feel good about the goal as a whole. And, intuitively, that makes some sense.

If we feel good that we can eat the way we’re supposed to, sleep the way we’re supposed to, train the way we’re supposed to, then why would we not feel good about our ability to run a marathon if it’s the product of these three behaviors, these three disciplines?

But in reality, we can’t average, we have to multiply if we want something that’s mathematically sound. And if we multiply 0.7 times 0.7 times 0.7, we find there’s only a 34% chance that we’re going to be ready on race day. We don’t know where we’re going to slip up, but the odds are we’re going to drop the ball in at least one of these three areas.

And I think that was the most surprising discovery for me writing the book was when I took it outside of the context of my own consulting work and into the world at large. And I think it’s an explanation for why we see so much failure in our world. In this example, we only need three things to go right. And we feel pretty good about each of them individually.

Now, imagine how many things have to go right for a business to be successful, for a merger to be successful, for a public policy to be successful. We start to understand how we can quickly experience a lot of failure if we’re not doing everything that we can to optimize our odds.

Pete Mockaitis
Yeah, I like that a lot. I was literally multiplying in my head as you were speaking like 34%. And, yeah, that is an eye-opening paradigm shift that illuminates a whole lot. And I’m thinking about this applies to just buying something. Like, if you have a lot of criteria for, let’s say we’re talking about food, “Okay, I want to eat healthy. Well, okay, well, it has to be organic and it has to be gluten-free and it has to have, you know, at least a third of its calories from protein.”

And then it has, there’s like two foods. There are two foods in the universe of food that meet my criteria. And it’s like, “Well, I’m not asking for too much,” but when you’re asking for all of those things at the same time, and most things don’t have any of your individual boxes checked, when you aggregate it, yeah, you narrow the field in a hurry.

Kyle Austin Young
It’s a good parallel and it explains or illustrates how important it is to try to design really straightforward paths to the things that we want. A lot of people are trying to wing it, “Oh, I’ll figure it out as I go,” but every time we add a new prerequisite to our success, we can dramatically reduce our odds of getting what we want.

So, it’s important to do what, I call it creating a success diagram, but write down, “What’s the goal? What’s everything that has to go right in order for me to achieve it?” and that’s the beginnings of having the ability to tinker and try to make sure that we’re optimizing to make this as streamlined as possible, because if we’re adding in steps that we could make work around with a better plan, we’re ultimately hurting our odds of getting a good outcome.

Pete Mockaitis
Now, it’s interesting when you spoke with the 70-70-70, you know, I’m a former strategy consultant from Bain and my brain just goes that way. I have a feeling, though, Kyle, you and I may be in the minority in this universe. Can you maybe get us oriented to your numbery probability worldview, if that doesn’t come naturally for folks?

Kyle Austin Young
Yeah, let me give you an example that has no numbers whatsoever, okay? So, when I first graduated from college, again, here’s a no numbers example, I wasn’t super excited about the entry-level positions that I was seeing. I wanted something more engaging, something more demanding, something with more responsibility, something with better opportunities for growth and career acceleration.

So, I did something really audacious. I was 21 years old, had a bachelor’s degree from the University of Oklahoma and I applied to be the product development director at a growing health organization. And, were I to win this position, I was going to be the boss for people who were in their 50s, 60s, 70s. Again, I’m 21. Some of these people have PhDs, master’s degrees. They’re experts in their field, and I’m applying to be their boss. So, a little bit audacious, but I got the interview, and I wanted to make the most of it.

Pete Mockaitis
No kidding.

Kyle Austin Young
So, at that point, what I did is I engaged in a habit that I call thinking negative. Most of the time when we’re pursuing big goals, people encourage us, “Think positive. Don’t worry about what could go wrong. If it’s meant to happen, it’ll happen,” or, “You’ll cross that bridge when you come to it.” I think that’s really, really bad advice.

I understand it. The fear is that if we identify these risks, maybe we’ll be so discouraged that we won’t move forward. I believe we have an opportunity to use our creativity to systematically de-risk our goals. So even at this time, before I was consulting, this was when I was just trying to get my first job out of college, I tried to identify, “What are the potential bad outcomes that could happen instead of what I want?”

And the reason for that is we can understand probability similar to how we traditionally understood matter. We pretty much all heard the phrase that, “Matter can’t be created or destroyed. They can just be transferred and rearranged.” And that’s true when it comes to probability. The odds of all the different outcomes that could happen add up to 100%.

So, if we want to make a good outcome more likely, we have to make the bad outcomes less likely. And one of the most straightforward ways to do that is by thinking negative, identifying the bad outcomes, and trying to reduce the risk of those things coming to life.

So, in the context of applying for this really important position, something that had the opportunity to really accelerate my career, I identified three potential bad outcomes. The first was that maybe the hiring squad would reject me because I looked so young and they were concerned there’s just no way that someone so young could lead this team. You know, understandable.

Well, what could I do in response to that? I couldn’t change my biological age, you know, I couldn’t do the Captain America thing and take the superhero.

Pete Mockaitis
Put a white beard disguise.

Kyle Austin Young
Yeah, well, that’s literally, half of that is what I did. Half of that is literally what I did. I was 21 years old. I looked like I was even younger than that. So, in preparation for the interview, I grew a beard and it just made me look several years older. It didn’t make me look as old as the people I’d be managing, but it at least took the edge off. I didn’t walk in looking like a little bitty kid.

So that was just a creative solution to try to de-risk that potential bad outcome. In the book, I call them PBO, another PBO that I identified was they might not want to hire me because of how flimsy my resume was. I didn’t have a lot of experience. I was fresh out of college. Again, I couldn’t change that. I couldn’t go out and get years of experience in preparation for this interview. But I could try to redirect the conversation.

And so, what I did is before the interview, I typed up a plan for all of the ways that I was going to try to reinvent and optimize this department. It became so thick that I had to have it spiral-bound, it was a book, and I took it with me and gave it to everybody I interviewed with.

And when they would ask me questions about my past, about my resume, I would just redirect it to become a conversation about the future, about the plan that I had for this department. And it, ultimately, took a lot of the pressure off when it came to not having a lot to show in terms of prior work experience.

The third potential bad outcome I realized, this is the last one I’ll give an example of, was that there was concern that I might not fit in with the existing team members. They might reject me thinking, “How is somebody young going to get along with these people who are so much older than he is? These people who are his parents’ age, his grandparents’ age, how is he going to be able to manage them effectively?”

So, what I did was a little bit creative. I asked an existing team member if the department had read any books lately, and she recommended a few different titles. And so, I went out and read all of them. And what that gave me the ability to do was speak this team’s language. I knew about their goals. I knew about some of the frameworks they were using and considering. I could make inside jokes.

I ended up in a group interview at one point where it was me and several other candidates who had gray hair, much older than I was, much more experienced, probably much more qualified. And I was running circles around them because I knew exactly what the team was up to. I made a joke at one point. There was a book out called The Whuffie Factor. It was about how brands can win social capital.

And somebody on the team presented an idea and I said, “I think that could bring us a lot of whuffie.” And I remember looking around, the other candidate’s eyes are bugging out of their heads, like, “What did he just say? What is he talking about?” But the existing team members were all laughing. They knew exactly what I meant.

So, at the end of all of this, I got the job. I became the product development director for this health organization at 21 years old. It all started by identifying what was going to have to go right. In this case, it was pretty straightforward. I just needed the offer. I already had the interview. But what could go wrong? What were the potential bad outcomes that could sabotage me getting what I wanted?

I identified three. I used my creativity to try to take as much risk out of them as I could. I tilted the odds in my favor and I walked away with a good outcome. I would later be laid off from that job, laid off from my next leadership position, and that’s what inspired me to start consulting. It was the diversification that it brought. But it was certainly something that set my career on a very different track than it would have been if I’d started in one of those assistants to the marketing manager roles.

Pete Mockaitis
Well, Kyle, that is a heck of a story. And I imagine that the people hiring you must’ve been scratching their heads, like, “Who the heck is this guy? Where did he come from? Are we crazy to actually consider this? But, like, we all saw the same thing. He was saying a lot more smart stuff than the other people. Nobody else had a spiral-bound opus master plan for what to do. So, in a way, it seems crazy to hire him, but another way, it seems crazy to not hire him.”

Were they open with you about this?

Kyle Austin Young
Oh, that’s exactly what happened.

Pete Mockaitis
Like, Kyle, “Here’s where we’re coming from, man. Here’s the deal.”

Kyle Austin Young
I got a call from one person, I think, it was kind of unsanctioned, and it was just him saying, “Obviously, we can’t offer you this job, you’re 21, this makes no sense.” But then I, just listening to him talk himself out of it. And so, I just sat there and it was about 30 minutes of him trying to talk himself out of voting to hire me.

I got an email from the CEO the day after that interview where there was a group interview. I just bumped into him in the hallway and, again, I’m crazy. So, I said, you know, “Hi, I’m Kyle. Here’s one of my spiral-bound plans for turning around the product development team,” and gave it to the CEO of the organization.

The next morning, I woke up to an email from the CEO, who I wasn’t really supposed to have even seen that day, and I thought, “Oh, this can’t be good.” And he said, “In my entire career, you’re the most prepared candidate I’ve ever seen.” And so, there’s this line in sales, I’m not a salesman by trade, but there’s a line that, “Selling is overcoming objections.”

And I see probability hacking as a similar discipline. Essentially, we have something that we want to happen, reality has some objections to that because our goal comes at the opportunity cost of all these other potential outcomes, and it’s our job to kind of sell life on the future that we want, try to overcome these objections, take these risks off the table, and make it where our path is the path of least resistance.

Pete Mockaitis
Yeah. Well, boy, you know, Kyle, this is a very exciting conversation. I feel like this whole body of work, this collection of ideas, has tremendous flexibility and power and implication. What comes to mind for me is, like, the 80-20 principle. Like, that’s just, like, eye-opening, game-changing, a wide array of things. And, boy, when you get it, things can be so transformative, it almost can feel like magic.

And so, boy, there are so many implications to this, but one I’m thinking about is that you got to get pretty specific, and you got to get pretty somewhat focused on a narrow-ish set of priorities. Because, Kyle, I mean, you can’t make a spiral-bound plan and read everybody’s favorite books for 20 interesting job opportunities. You got to kind of narrow the playing field in order to go all in on that thing and create unheard of results.

Kyle Austin Young
I think that’s true. I think that, in that specific example, had I been applying for 20 jobs that I wanted as bad as I wanted that product development director job, there could have been some challenges. Now, I would, in a friendly way, counter and say that I think some emerging technologies are making that more possible than ever.

We now have tools that can help us create proposals much more quickly than we could when I was applying for my first job out of college. We now have tools that summarize books for us and give us the opportunity to digest the key insights from a piece of content a lot faster than we would have, otherwise.

But, yes, you’re absolutely right that it starts with a goal. It starts with getting really clear on what you want, and, in that context, you then have the opportunity to optimize your odds. One of the reasons why I think that’s really important also is when it comes to asking for advice. I’ve, historically, this sounds arrogant, but I’ve historically been kind of opposed to asking for advice, and it’s not because I think I know everything, not by a long shot.

But what I found is a lot of people’s advice is unapplicable in ways that sometimes can even be confusing. And I’ll tell you a story about that. One time, I was considering taking on this new consulting client and it was going to be a huge retainer, lots and lots of money. But this was also just a notoriously difficult person. It was going to be a really stressful engagement if I chose to take it on. And I wasn’t sure what to do.

So, I decided to reach out to some peers and colleagues and ask them what they thought. And, originally, I was really frustrated because it almost split down the middle. About half of them told me, “Take the money,” and about half of them told me, “Why would you want the stress?” And at the time, I just thought, “How am I going to be able to make heads or tails out of this advice?”

And, finally, I noticed a trend. And the trend was that the people who I asked who had significantly less money than I did, almost unanimously said, “Take the job. Make the money. Why would you not?” And the people who I asked who had a lot more money than I did, almost unanimously said, “Why would you enter into such a stressful contract just in exchange for a paycheck? You don’t need that money. Go make it somewhere else.”

And what that taught me was these people weren’t really giving me advice in the context of what I wanted, in the context of my opportunities and limitations. They were giving me advice from their own context. The people who wanted money told me, “Go get the money,” and the people who wanted to avoid stress told me, “Go avoid the stress.” But that wasn’t really something that accounted for my priorities.

So, I encourage people to create a success diagram, which includes everything we’ve talked about. What’s the goal? What’s everything that has to go right for you to achieve it? For each thing that has to go right, what are the things that can go wrong?

And what’s powerful for that is it creates a context. It creates a context that allows me to ask other people for advice because now we’re on the same page. It creates a context that allows me to collaborate with other people who might be participating in the project. I can now delegate, I can brainstorm, I can say, “Here’s what we’re pursuing, here’s what has to go right, here’s what could go wrong.”

“Kevin, what can you do about this risk over here? Felicia, what can you do to help us take the risk out of this other potential bad outcome?” We now have the ability to have a shared text and, ultimately, it makes us a lot more effective when we’re pursuing big goals.

It also just gives us a way to store information. So, just as you mentioned, as the context changes, as we get new information, we have a place to put it where we’re constantly getting smarter over time and we can get that focus that you described.

Pete Mockaitis
Well, Kyle, this is such good stuff. Walk us through the whole thing in depth. So, we’re talking about the diagram. You just keep talking.

Kyle Austin Young
Well, you know, ultimately, what I teach in the book is I think that there’s been this cultural narrative that there’s two types of people who succeed. People who are really talented, connected, privileged, and people who get lucky. I don’t think that’s a very good understanding. It doesn’t take probability into account at all.

I think there’s four paths to success. I think some people succeed in spite of really bad odds because they get lucky. I tell the story in the book of Norma Jeane Dougherty. She’s working at an aviation munitions factory during the war when a photographer comes to take pictures for a military magazine. He notices how pretty she is.

He says, “Would you be interested in potentially having a career in modeling, be on some magazine covers?” She says, “Sure.” Quits her factory job, has a successful modeling career, and then, ultimately, has a really successful acting career under the stage name Marilyn Monroe.

Now, that’s a cool success story. Good for her. But if you met somebody who is an aspiring actress, would you reverse-engineer Marilyn Monroe’s story?

Pete Mockaitis
“Here’s what you got to do. Just get discovered on your job and then…”

Kyle Austin Young
“Step one, we’re going to need to get you a job at an aviation munitions factory because that’s what Marilyn Monroe did.” No, you wouldn’t. She, undeniably, achieved enormous success, but she did that, overcoming really bad odds. She got lucky, right?

So that is one of the paths through which people succeed. And it’s important to acknowledge that because it explains some of the success stories in our world that people have had such a difficult time reverse-engineering. It might not be as obvious as Marilyn Monroe, but there are stories where we’re out there, you know, “Oh, every CEO drives a blue car. Buy a blue car and you’ll be a CEO.”

No, you won’t. That’s unrelated. There’s no causation there. They just like blue cars. It has nothing to do with that. So, it’s important to understand that some people are succeeding through luck. It’s important also to understand that we have the opportunity to experience more luck in our lives when we recognize that you don’t always have to beat the odds, sometimes you can play them.

One way that you can overcome bad odds is through the power of multiple attempts. I interview entrepreneurs for the book, like Apoorva Mehta who founded Instacart. Instacart experienced enormous growth during the pandemic because people were at home, they couldn’t go to the grocery store, and grocery delivery was in exactly the right place at the right time.

I think it was, don’t quote me, I could find the number, I believe he said it was a $9 billion increase to their valuation. Just absolutely remarkable what they were able to achieve. So, you hear that, you think, “Wow, how could anybody be that lucky to be in exactly the right place at the right time?”

Then you learn that Apoorva Mehta started over 20 businesses before Instacart. And you think about these numbers in our heads that nine out of 10 businesses fail. Well, we would expect a couple of his businesses to be successful. Maybe not nine billion in ten months, but, all of sudden, these odds have changed because of the power of multiple attempts.

In the book, I also talk about Thomas Edison. Thomas Edison was in a race to develop the first practical incandescent lamp, and he’s, ultimately, competing for this really valuable patent that could change the trajectory of his career, but he’s not the only person trying to do this. All of them are struggling to find a filament that can get hot enough to glow without catching on fire or snuffing out, not being worth the effort.

What he did that was different than these other inventors, was he experimented with 6,000 different plant materials, and he ultimately finds that carbonized bamboo, which would not be my first guess, is this nearly ideal filament for what he was looking for. He gets this patent. It helps him achieve enormous success in his career. So, some people are succeeding because of the power of multiple attempts, and I give some examples of that.

Other people are succeeding because they choose to, very intentionally, pursue goals where their odds are good. And I think there’s a lot of wisdom in that, too, to recognize that we have areas of strength, and that because of those areas of strength, we have an opportunity to choose goals that are more likely to succeed. And then success tends to beget success in other areas.

I give the example in the book of people who want to play in the National Basketball Association, just to illustrate how our attributes can change our odds. If you’re shorter than six feet tall, and the average US male is 5’9″, I’m 5’11”, so I’m under six feet tall, then your odds of playing in the NBA are one in 1.2 million. So that’s terrible odds. Terrible odds.

But here’s what’s really interesting. If you’re between six feet tall and six foot three, your odds go up to one in a hundred thousand. If you’re between six four and six seven, it’s one in eight thousand. Between 6’8 and 6’11, 1 and 200. And this is what knocks people over if you happen to stand over 7 feet tall, if you’re over 7 feet tall, your odds of playing in the NBA are actually 1 in 7. One out of every seven people over seven feet tall is playing in the National Basketball Association.

Pete Mockaitis
The rule of seven.

Kyle Austin Young
At least in the United States of America, yeah, you’d line them up. And that’s pretty incredible to think about, that as we just got incrementally taller, our odds changed and changed and changed. And by the end of it, we went from one in 1.2 million to one in seven.

So, there’s real power in taking stock of, “What are the areas where we do have strength? What are the areas where we do have advantages? They might not be the goals that we’re most excited about right now, but could pursuing some of those goals lead to opportunities down the line?

You know, I’m really thankful to have this book deal. One of the things that made that possible was, first, writing for sites like Harvard Business Review and Forbes. Those were smaller accomplishments, but they brought bigger accomplishments within reach.

And then the fourth path to success is what we’ve described. It’s probability hacking. It’s taking the odds we have, thinking negative, identifying bad outcomes, and using our creativity to ultimately make those odds better.

In some ways, we can layer those onto the other three paths. We can use it to get lucky more often. We can use it to reduce the number of repeated attempts that we might need. We can use it to make more goals, things that actually look pretty good from an outlook standpoint. So that’s more or less how I think about this.

Pete Mockaitis
Okay. Well, so thinking about your second chapter, “Understanding Your Odds,” I mean, you had a delightful bit of research there about the NBA. How does one go about knowing the odds given, by definition, the future is not completely knowable? So, I mean, I could just make up some numbers in a spreadsheet, but how do I get those?

Kyle Austin Young
It’s a fair question, and I’m very transparent about the fact that this is going to be an estimate. You have to kind of choose between two different realities. You can turn to base rates, which don’t typically take your individual attributes into account. They’re normally a guess. Often, odds are dramatically misreported. Some of the things that, you know, considered understood to be absolutely true aren’t even close to that.

I bring in a couple of news headlines. Here’s three. These are real-life headlines published by actual news outlets. One of them is, “Texas man survives one in a million chance of being struck by lightning.” Another is, “One in a million chance, Salado couple’s car struck by lightning.” Another is, “The odds of getting struck by lightning are one in a million. Wednesday, it happened three times in Wichita.”

One of those stories actually features a quote from an emergency room doctor affirming the idea that your odds of being struck by lightning, actually the exact quote is, “Your chances of being struck by lightning are roughly one in a million.” But according to the National Weather Service, the actual number for the average American is one in 15,300.

It’s not one in a million, not even close to one in a million. The closest I could come to explaining that one in a million number is that’s roughly your odds in any given year, but it’s not your odds over the course of a lifetime.

Pete Mockaitis
Well, I think you’re being generous, Kyle. I think no one really thought about it. They just say, “It’s really rare, so we’ll call it one in a million.”

Kyle Austin Young
Yeah, sure, it’s a one in a million thing. We love the number one in a million. It’s one in a million. I give the example. I share a short story that’s about someone who dies in a tragic bicycle accident. It’s fictional, but the phrase one in a million comes up. And, okay, sure, dying in a bicycle accident, one in a million. Surely, right, I mean, that has to be so rare. According to the National Safety Council, one out of every 3,546 Americans will die in a bicycle accident.

So many of these numbers that are circulating in our world are just made up. They’re misreported. They don’t take our individual attributes into account. Sometimes they’re weighed down by people who made bad decisions.

When we think about the odds of a new product succeeding when it’s released to the market, there are rates for that based on research. But then you think about projects like Bic for Her, which was a line of writing pens that were marketed to have a thinner barrel to fit a woman’s hand.

Pete Mockaitis
Yeah, women need that.

Kyle Austin Young
Yeah, women need a thinner pen so that they can write effectively. And this product got laughed out of the market, pretty quickly discontinued, but there were significant investments made to release this product.

And so, when you think about that, if they were to just do even a little bit of keyword research, I give some examples in the book, they could find pretty quickly that no one was looking for pens for women. That wasn’t a desire. There were people looking for a lot of other types of pens that could’ve been potentially a better opportunity if they were to release a product in that space.

And so, base rates are also weighed down by people who made decisions that you probably wouldn’t make, right? We look at how many failed products there are. Well, we found that the number one cause of failed product releases, according to some data by CB Insights, is a lack of, they call it no market need. It’s just a lack of demand.

Pete Mockaitis
Yeah, nobody wants the thing.

Kyle Austin Young
Yeah, nobody wants the thing. So now we’re thinking about, “Well, base rates say that most of the products that get released failed.” Okay, but is that because people are releasing things that they never took the time to validate at all? If I take the time to validate demand for my product or service, my odds are very different.

So, ultimately, you ask the question, “Where do these numbers come from?” And you have to make a choice. You can turn to base rates, which have a number of flaws, or you can estimate. And what the leading forecasters in the world do is they will typically try to break big predictions about world events into smaller ones.

Instead of saying, you know, “What are the odds of this war happening?” they’ll say, “What are the odds that this country experiences an affordability crisis while this other country experiences a surge in nationalistic pride?” whatever the case may be. They try to break it down into the component parts, the ingredients that could lead to a conflict like that or to a good outcome, depending on what they’re predicting.

And when we break that down in the context of our goals, I find that we have an opportunity to make predictions that can be, in some ways, an antidote to overconfidence. If we go back to that idea of running a marathon, we need to eat, sleep, and train according to specific regimens for 90 days, what’s the base rate that says whether Kyle will stick with his diet for 90 days? I mean, I’m Kyle. Like, there’s no statistician running the numbers on that.

So, to some extent, there is an expectation in the context of these very individualized and personal goals that we’re going to have to make some estimates. But by breaking them down into the component parts, and then being informed by base rates, letting them challenge our assumptions, I think we have an opportunity to deepen our understanding of how likely we are to get what we want.

And again, beyond that, by probability hacking, by using our creativity to take the risk out of these goals, we have an opportunity to improve our odds of success. And that’s what I think can change our lives.

Pete Mockaitis
And I’m curious, do you have any rough numbers for starters that you like to hang your hat on or base level assumptions? Because, for example, when I’m considering a business initiative, it’s like, “I have no idea if this thing is going to work out.” It’s like, “But it seems like a good idea to me.” But historically, you know, the slight majority of “seems like a good idea to me” things did not work.

So, my base level assumption is like, “There’s a 30% chance that this thing will work out.” And then I like to see, “Okay, well, given that,” this is why I think you and I are simpatico. It’s like, “Well, given that, is it worth the time and money to embark upon this risky path, knowing there’s a less than one in three chance it’s going to work out?” And it’s like, “Well, heck, yes, it is because the upside is so substantial within. Well, then game on, let’s do it.”

So, I found that quite helpful, it’s just like put that in a spreadsheet and mapping it out. So, 30%, it’s a little bit arbitrary, a little bit made up, but it’s kind of based on my own experience, so there’s more than nothing in terms of the evidence supporting it. So, do you have any rules of thumb, guidelines, numbers that find their way into your estimates often?

Kyle Austin Young
Sure. I’m not a financial advisor. I can’t give investing advice, but I can say that I tend to be more risk averse than most people do. I hate losing money. I just almost can’t stand it. So, I want to be pretty confident that a goal is going to be successful.

And how do I get a sense of that? Well, I create a success diagram and I try to look for gaps in my thinking. I, then, again, have a context for asking for advice. I can go to people who know more than I do and say, “Are there bad outcomes I’m not considering or bad outcomes that I’m not taking seriously enough? Is there a more straightforward path to what I want?”

The thing that I find encouragement in. There are two things, actually. One is, you mentioned earlier that this isn’t really intended to just be a step-by-step framework, that that’s part of it, but it’s really a way of thinking and a suite of tools that we can use situationally.

Sometimes we might want to leverage the power of multiple attempts. Other times we might want to create a success diagram and try to do everything we can to minimize the risk of potential bad outcomes. We can do that in real time at every step in the process.

So even if we need to pivot, even if we think we need department manager A’s approval, it turns out we’re going to need department manager B’s approval. Great. What are the reasons that that person might reject what we’re, ultimately, offering?

So, there’s an opportunity to do this work as we go and improve our odds. And the knowledge that I have the ability to do that is one of the things that gives me confidence that even when uncertainty arises, even when unexpected speed bumps get in my way, I know how to change my odds, and that’s something that I find encouraging.

The other thing, though, is I encourage people not to think of our goals necessarily as pass/fail. Even if we don’t accomplish the original outcome, we can sometimes accumulate assets and resources that can be repurposed.

In the book, I tell the story of this group of friends who, I believe they just left jobs at PayPal when they don’t, I’m pretty sure it was PayPal. I’m not 100% positive. They decided to start this new dating website at a time when the internet was much younger or much newer, and it was difficult to upload content to the internet. It just wasn’t something that many people had the tools or the skills to do.

And one of the ways this dating site planned to differentiate itself was it was going to make it really easy for people to upload a video introducing themselves, and then put themselves in a position to meet people who might want to go on a date with them. And that was a pretty clever differentiator at that time.

The challenge was they just couldn’t get people to do it. It was a time when it was a new tool, privacy concerns were a little different back then, the idea that I was going to upload a video of myself to the internet for strangers to watch to consider whether or not they wanted to go on a date with me, that sounded crazy. Now we put content of ourselves online all the time, but that was a concern.

So, ultimately, this dating website fails. But this group of entrepreneurs didn’t give up on the idea. They instead stopped and asked the question, “What assets and resources have we accumulated through the work that we’ve already done?” And one of the biggest things was they’d use their programming skills to develop this incredible tool for uploading videos to the internet, something that was really difficult to do at the time.

So, they pivoted a little bit to a new goal, which was, “What if we started a website where anyone could upload videos about anything they wanted to?” And they call it YouTube. They end up selling it for one and a half billion dollars, and it becomes this thing that changes their lives. And so, you asked the question, “At what number is something a go for me?”

Well, I’m more risk averse than most people are, but I know I can change my odds over time. And I also don’t necessarily view failure the exact same way, because I know of a failed dating site that made over a billion dollars.

And so, I think there’s typically opportunities when we have a success diagram to be able to collect, or rather remember and process, “Here’s all of the resources that we’ve been able to get our hands on as a result of the work we’ve done.” We’re not finishing where we started, even if we’re not finishing where we wanted to.

Pete Mockaitis
So good. Well, so, Kyle, we’ve said the words success diagram a few times here. Can you tell me, literally, pen to paper, what does my success diagram look like?

Kyle Austin Young
Your success diagram starts with the goal you want to accomplish. That’ll go on the right side of the page. And then you will make a list leading up to it of the steps that are going to have to be achieved in order to accomplish it or the things that have to go right. Sometimes it’s not linear per se. Sometimes it’s just, you know, the ingredients in success, like in that training for a marathon example.

It’s not that we’re going to eat a certain way, and then we’re going to sleep a certain way, and then we’re going to train a certain way. In reality, it’s that we’re going to be doing three things simultaneously that we’ve been told can lead to success. So, there is a template.

This will get better over time, but I wanted to give people something because it’s a question I get a lot. If you go to SuccessDiagram.com, there’s a free template that you can just print. You don’t have to buy my book or anything like that. You don’t even have to give your email address. It just makes it really easy for you to fill in, “Here are some of the critical points on the path to my goal. Here are some of the things that might go wrong.” So, that’s something you could certainly take a look at. It’ll be helpful for you.

I know that podcasting, you know, it’s a little bit tricky with an audio discipline to paint a word picture for you, but I typically draw a circle for everything that has to go right. I write the thing in the center of the circle, one at a time, goals at the end of the list, and then beneath each thing that has to go right, I just make a list of the potential bad outcomes that could ultimately sabotage my success.

Pete Mockaitis
All right. Well, Kyle, tell me, anything else you want to make sure to mention before we hear about a few of your favorite things?

Kyle Austin Young
I want to talk about my favorite things.

Pete Mockaitis
All right, let’s do it. Can you start with a favorite quote?

Kyle Austin Young
You know, one of the real privileges of writing this book was I got the opportunity to interview Jack O’Callahan who played for the U.S. Men’s Olympic Hockey Team in 1980 during the “Miracle on Ice” when the United States beat the Soviet Union, this very unlikely victory.

He has this, I wouldn’t call it a quote, they used it as a quote in the movie version, but he says that he doesn’t remember exactly what was said by his coach Herb Brooks in the locker room before the game.

But he says he remembers leaving the locker room to take the ice with the impression that what his coach had said was, or tried to communicate, was, “If we played these guys 10 times, they would probably beat us nine times, but they aren’t going to beat us tonight.”

And that’s a quote that means a lot to me, because it acknowledges that we often are up against goals where our odds aren’t very good, but through the power, in my opinion, of multiple attempts, we have the opportunity to persist, achieve success, and then dramatically change our odds on subsequent pursuits.

And if we go into each one of those, recognizing that we’re going to fail maybe even more than we succeed, depending on how audacious the goals we’re pursuing are, but this mindset, “They’re not going to beat us tonight, that we’re going to do everything we can to make this the time that we ultimately find success,” I think we put ourselves in a powerful position.

Pete Mockaitis
And a favorite study or experiment or bit of research?

Kyle Austin Young
I’ve already mentioned this one, but I think that one of my favorites is just the story of Thomas Edison because what I love about his story is a lot of people have this idea of kind of decision overwhelm, that, “If there’s too many options, we’re going to be paralyzed and we won’t know what to do.” I can understand why people would feel that way.

What I think the opportunity is when we’re making decisions like that is we just need to find a standard to measure the ideas against. And in his case, it was just, “Which one of these filaments glows the longest without burning out or without catching on fire?” And that allowed him to sift through 6,000 different ideas, and it wasn’t overwhelming. He just had a stopwatch. It’s just, “Which one of these accomplishes the goal?”

And so, I think a lot of people who are struggling to weigh their options and make a decision that they’re proud of are doing that because they haven’t really defined what success looks like. If we know what success actually looks like, we can hold our ideas up against it, and, all of sudden, it becomes a lot easier, in my opinion, to identify the one that makes the most sense in our context.

Pete Mockaitis
All right. And a favorite book?

Kyle Austin Young
I’ll tell you book that I think pairs really well with mine. It’s a book by a friend and colleague, Dr. Ron Friedman, it’s called Decoding Greatness, and he takes the idea of reverse engineering and brings a framework to it. It’s basically, “How can you take great work, completed by other people, and use it to improve your own performance?”

And I think it’s a really nice pairing with my book because, ultimately, if you have a framework for learning how to do things that comes from studying others, and then you have a framework for improving your odds of success, then I think you’re in a pretty strong position.

Pete Mockaitis
All right. And a favorite habit?

Kyle Austin Young
A favorite habit for me is thinking negative. I’m sorry to be an Eeyore, but I think that the idea that positive thinking is an antidote to risk just doesn’t make any sense, the idea that I can somehow wish something into existence. I think there’s tremendous value in focusing on what we want.

I think there’s tremendous value in that sense of kind of manifesting what our intentions are because when we’re really clear on what the goal is, it helps us sort through the information that we experience in life. We know who to talk to at a networking event. We know which news headlines to pay attention to and which might not be relevant to us. So, I totally value and appreciate the level of focus that I think is implied there.

But for me, tell me how if I’m training for a marathon, positive thinking is going to keep it from raining on a day when I need to run, to tell me how wanting to run a marathon is going to prevent shin splints? It just doesn’t work like that. We have the opportunity to think negative, identify the things that could go wrong, and use our creativity to systematically de-risk our goals.

Pete Mockaitis
All right. And is there a key nugget you share that really seems to connect and resonate with folks, they quote back to you often?

Kyle Austin Young
Probably you don’t have to beat the odds. Well, sometimes you don’t have to beat the odds. You only have to play them. Obviously, there’s goals where that doesn’t apply. I talk about the story of someone trying to graduate from college, and some people have better odds at that than others do.

And it wouldn’t make sense for someone with bad odds to enroll in four different universities and hope that they’ll complete one of the four programs. So, there’s certainly exceptions to that. But in many goals, one of the most reliable ways to overcome bad odds of success is through the power of multiple attempts.

Can I tell one last story very quick?

Pete Mockaitis
Oh, yeah.

Kyle Austin Young
In the book, I talk about Ben and Jerry’s. Ben and Jerry’s was this upstart organization that wanted to enter into the really crowded industry of ice cream sales. And at that time, and also today, the best-selling ice cream flavor in the world is vanilla. It’s really hard to make a vanilla ice cream that’s so much better than everyone else’s that they leave their favorite ice cream brand and come over to your company, right?

So, they decided to do something different. They said, “We’re going to try to make exotic new flavors that no one’s ever heard of before. And it’ll be so provocative that people will say, ‘Well, I’ve got to try that.’ And if they like it, we’ll be the only place they can get it because no one else has these crazy flavors that we’re dreaming up.”

But that’s an unreliable strategy, at least in the context of one attempt. It’s hard to guess what bizarre ice cream flavor enough people are going to like and want to actually try. So, what they did is they entered into a model where they knew that failure was going to be a big part of it, and they resolved to celebrate those failures.

And so, if you ever go to the Ben & Jerry’s factory in Waterbury, Vermont, I’ve been personally, outside, they have what they call the flavor graveyard, and it has actual headstones with these little funny epitaphs for failed ice cream flavors that they’ve had over the years. They have over 300 discontinued flavors of ice cream.

But recognizing that that was going to be part of the game is what allowed them to, ultimately, uncover classics that made them the best-selling ice cream brand in America for many years.

Pete Mockaitis
And, Kyle, if folks want to learn more or get in touch, where would you point them?

Kyle Austin Young
If you want to grab a copy of the book, you can do that pretty much anywhere – Amazon, Barnes & Noble, Target, directly on the Penguin Random House website. If you want to learn more about me, you can go to my website, KyleAustinYoung.com.

But if you want to connect, then find me on LinkedIn. That’s been one of the fun surprises about this journey is, at first, I wasn’t asking for that specifically, but people would find me on LinkedIn after some of these interviews and reach out. And it’s been a lot of fun to have those conversations. So now I’m just trying to shorten the path to that. If you have any questions, send me a message.

Pete Mockaitis
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Kyle Austin Young
I would encourage you to try to create one success diagram for a goal. I would encourage you to try to see what it looks like. You’re not going to have all the facts, and, in some cases, that means you won’t want to rely on predictions that would come out of it, but you’re now going to have a tool that allows you to collect information, add it over time.

And when you create diagrams for various goals that you’re considering, you can start to make decisions around which one makes the most sense in your context. In so many cases, when people are trying to prioritize a goal, they’ll sometimes ask the question, “Which one aligns most with my values?” or, “Which one sounds like the most fun?” or, “Which one do I think will bring other opportunities within reach?” All those are great questions.

But if we aren’t stopping to also consider our odds of success, then why does it matter how much alignment there is if the goal’s almost certainly going to fail? I think that we need probability to have a seat at the table. Certainly, there’s goals like curing cancer, where even when the odds are bad, we need to keep trying to do it.

But in the context of our careers, I don’t see any reason to invite that level of risk. Let’s find the goals that are most likely to have a good outcome and then ask questions like, “Where is there the most alignment?”

Pete Mockaitis
All right. Kyle, thank you.

Kyle Austin Young
Thank you.